Derivatives of pyridine and quinoline. LXXII. Reactivity of bromine atoms in brominated pyridines. Action of sodium phenate on 2,4,6-tribromopyridine was written by den Hertog, H. J.;de Jonge, A. P.. And the article was included in Recueil des Travaux Chimiques des Pays-Bas et de la Belgique in 1948.COA of Formula: C11H9NO This article mentions the following:
VI (3 g.), 0.25 g. Na, and 20 g. PhOH are heated 24 hrs. in a sealed tube at 145-50°, and the contents of 3 tubes poured into 300 cc. 15% NaOH and extracted with Et2O. Washing (NaOH) and drying (Na2SO4) the Et2O give 0.7 g. mainly VI, b0.7 110-25°; 0.9 g., b0.9 135-45°, which, washed with alc., gives 0.5 g. undissolved VI and 2,4-dibromo-6-phenoxypyridine (X), m. 41.5-2.5°, by evaporating the filtrate; 4.5 g. X, b1 153-61°, m. 37-41°; and a 4th fraction, b1.4 165-85°, which, washed with alc., gives a residue of 4-bromo-2,6-diphenoxypyridine (XI), m. 88-92°. VI (2 g.), 0.3 g. Na, and 20 g. PhOH, heated in a sealed tube 24 hrs. at 195° and poured into aqueous NaOH, give 1.3 g. (60%) XI, m. 93-4°. Similarly, 2 g. 2-bromopyridine, 0.5 g. Na, and 12 g. PhOH give 1.4 g. (70%) 2-phenoxypyridine (XII), m. 42-4° [XII and alc. picric acid give the picrate, m. 104.5-5.5° (from BuOH)]. 2,6-Dibromopyridine (XIII) (1 g.), 0.2 g. Na, and 12 g. PhOH give 1 g. crude 2,6-diphenoxypyridine (XIV), m. 60-1° after sublimation in vacuo; 1 g. 2,4-dibromopyridine, 0.5 g. Na, and 20 g. PhOH give 95-100% 2,4-diphenoxypyridine (XV), m. 87.5-8.5° (picrate, m. 140-1°, from picric acid-BuOH); and 1 g. VI, 1 g. Na, and 20 g. PhOH (36 hrs.) give 2,4,6-triphenoxypyridine (XVI), m. 79-9.5°. X (0.66 g.), 0.2 g. NaOH in alc., and 0.15 g. PdCl2 absorb the calculated amount H in 20 min.; evaporation of the filtered solution gives, on pouring the residue into H2O and ice-cooling, XII, m. 37-40°. VI (9 g.), 2.7 g. PhOH, 1.2 g. NaOH, and 9 cc. H2O, heated 24 hrs. at 150° in a sealed tube, and the lower layer made strongly alk. and extracted with Et2O, give, on drying and distilling the Et2O, 2.2 g. VI, b0.7 130°, and 3.5 g. semisolid, b1.5 140-65°, which, filtered through a glass filter, gives 1.2 g. 2,6-dibromo-4-phenoxypyridine (XVII), m. 84.5-5.5°; the filtrate, cooled and filtered, gives 1.3 g. crude X, m. 33-8°. Hydrogenation of XVII as described above and petr. ether-extraction of the aqueous NaOH-diluted residue gives 4-phenoxypyridine, m. 40-3°, identical with that (m. 45.5-6.5°) prepared according to Königs and Greiner (C.A. 25, 3998); picrate, m. 171.5-2° (from alc., then BuOH). Hydrogenation of XI gives XIV, m. 59.5-61°. XIII (4 g.) and 15 cc. 40% aqueous PhONa, heated in a sealed tube 10 hrs. at 150°, give, after recrystallization from 50% alc., then petr. ether, 75-80% 2-bromo-6-phenoxypyridine, m. 86.5-7.5°. XVII (0.8 g.), 0.055 g. Na, and 15 g. PhOH (sealed tube, 195°, 24 hrs.) give, on extracting the basified mixture with Et2O and evaporating the Et2O, a semisolid which, filtered, gives 2-bromo-4,6-diphenoxypyridine (XVIII), m. 87-8°. Hydrogenation of XVIII gives, on evaporating the filtered solution, basifying the residue, extracting with Et2O, distilling the Et2O, and treating the residue in BuOH with picric acid-BuOH, the picrate, m. 141-2°, of XV. X, XI, XII, XIV, XV, XVI, XVII, and XVIII are recrystallized from petr. ether. In the experiment, the researchers used many compounds, for example, 2-Phenoxypyridine (cas: 4783-68-0COA of Formula: C11H9NO).
2-Phenoxypyridine (cas: 4783-68-0) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.COA of Formula: C11H9NO